Formaldehyde → 11-Dodecen-1-ol

Participants

Reaction Steps

This example illustrates a synthetic protocol for inventive compound no. 2525 (see above for chemical name and formula). To a suspension of magnesium (6.4 g, 265 mmol) and a crystal of iodine in tetrahydrofuran (40 ml) was added 10-undecenyl bromide (Syn. Comm. 1984, 14, 591-597: 12.25 g, 53.0 mmol) in tetrahydrofuran (30 ml) over 30 minutes and the reaction was stirred for a further 30 minutes after the addition was complete. The solution was added via a canula over 5 minutes to a suspension of paraformaldehyde (1.80 g, 60.0 mmol) in tetrahydrofuran (40 ml) and stirred at 25° C. for 16 hours. Saturated ammonium chloride (80 ml) was added and extracted with diethyl ether (2×100 ml). The combined organic extracts were dried (magnesium sulfate) and evaporated to give a residue which was distilled at 2 mm Hg, yielding a clear liquid alcohol, 11-dodecen-1-ol (6.53 g, 67 %, b.p. 105°-107° C.).

Provenance & Evidence